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8 Insider Tips to Have the Best Chicago Experience Ever

Get the most out of your trip to this beloved city this summer.

Chicago has long been my favorite city on Earth. So much so, that the instant I was able to move there, I did. To my surprise, despite being the third-largest city in the country, Chicago is often a destination that even travel writers have told me they've never visited. It doesn't have the glitz of Hollywood or the bright lights of Times Square, but Chicago is a city that's definitely worth visiting.

From having over 200 theater companies, dozens upon dozens of festivals, and being called the Best Bike City in America, Chicago is a unique place. Here are some tips to ensure that you have the best Chicago experience ever–and have the chance to really get to know the Windy City. And next, don't miss 10 U.S. Islands to Add to Your Bucket List—No Passport Required.

Check out some one-of-a-kind spaces.

The Bean in Chicago, Illinois

Okay, yes, there's The Bean (actually named Cloud Gate) in Millennium Park. It's the shiny art piece tourists love to see downtown. But Chicago has much more interesting sights than this reflective orb that could use a good Windexing. A few minutes walking distance away from The Bean is the Chicago Cultural Center. This gorgeous piece of architecture, from 1897, hosts all kinds of events to partake in too.

You can hang out in The Green Mill, a cocktail lounge and jazz club that was frequented by Al Capone during Prohibition. Check out the mesmerizing Auditorium Theatre which opened in 1889 and remains an absolutely enchanting space. Frank Lloyd Wright even once called it "The greatest room for music and opera in the world–bar none."

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Get a transit pass.

Chicago transit system subway

Basically anywhere you go in the world, so long as it has public transportation, the advice will often be to utilize the transit system. Chicago is no different. The Chicago Transit Authority (CTA) is how Chicagoans generally get around if we aren't biking or walking. From the trains to the busses you can get around fairly reliably with this system.

Your best bet, especially if you plan on having a packed itinerary, is to get a multi-day pass. In 2022 the 3-Day unlimited CTA pass for both busses and trains is only $15. Plus with the Ventra phone app, you don't even need to buy a physical card. And you can keep track of wait times with the Transit Stop: CTA Tracker app.

Don't miss the museums.

The Field Museum in Chicago

Chicagoland has no shortage of museums. According to Museum Hack, there are 67 as of this year. These museums aren't your run-of-the-mill locations either. Chicago's museum collection has some world-renowned places. The Field Museum is one of the largest natural history museums in the world with a building dating back to the 1893 Worlds Fair. That's why both the Field Museum and the Museum of Science and Industry are both such works of art in addition to having such remarkable collections.

Chicago is also home to the country's first independent museum of Black culture. The DuSable Museum of African American History is visual splendor on top of being an important curator of cultural preservation. Some other unique museums you can find here include the American Writers Museum, The Art Institute of Chicago, Adler Planetarium, and the Museum of Contemporary Art. We are very proud of the cultural institutions we have here in the Windy City.

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Take advantage of a walking tour.

lion statue chicago illinois famous state statues

No matter what you're interested in learning about in Chicago, there's probably a walking tour for it. From haunted spots, architecture tours or prohibition crawls, walking tours abound in Chicago. When you're in a walkable city, it's easy to see a lot in a short amount of time.

One tour can even take you under the city to explore the Pedway. That's right! Chicago has its very own underground tunnel system. Can you blame us? Try walking through the wind tunnels of downtown in February when the windchill is -30 degrees. It isn't fun. But seeing the fascinating tunnel system is fun!

There are also a lot of free walking tours available. Free Tours by Foot is an excellent tour company with a variety of offers throughout the year. Tour guides from this company can also be hired for private tours as well.

Spend some time on the river.

chicago cityscape over the river

Not only does Chicago get to sit beside the picturesque Lake Michigan, but we also have an expansive river system that runs right through the city. The city's relationship with the river has been complex through the centuries which you can learn all about on one of the myriad river tours offered by Chicago boat operators.

In fact, The Chicago Architecture Center River Cruise was even named the best boat tour in North America in 2021. This river cruise is one I've taken several times. You learn all about the city's magnificent architecture as well as its history from a team of experts. Other cruises you can take along the river include cocktail cruises, history tours, and even themed tours like the various fireworks tours in the summer when Navy Pier lights up the night sky.

See a show (or three).

Chicago Theater
f11photo /

This is a shameless plug for Chicago's theater scene. In addition to being a travel journalist, I'm also a theater journalist. Since moving to Chicago Ive seen hundreds of performances and will staunchly defend Chicago as the best theater city in the world. This city has over 200 theater companies because it can also sustain them. From the renowned Steppenwolf and Goodman Theatres to Teatro Vista and Broken Nose Theatre, there truly is something for everyone to see here–no matter what time of year.

Plus Chicago is home to improv companies like The Second City which has cemented this city as the birthplace of modern improvisational comedy. Fun fact: Second City's namesake is borrowed from Chicago's other big nickname, The Second City. Chicago is so named because the first city burned down in The Great Chicago Fire.

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Get to know the neighborhoods.

Elevated view of Hyde Park with Anzac War Memorial at dusk, Sydney, NSW, Australia

Truth be told, most Chicagoans don't live downtown. With 77 community areas in the city, most of us live in other neighborhoods. Each of these neighborhoods has its own style and identity too which makes them really fun to explore. If you really want to get to know Chicago, seeing our neighborhoods is the best way to do it.

From the city's northernmost neighborhood Rogers Park (my home) you'll get a taste for eclectic and artsy folks. Whereas down in one of the city's southernmost neighborhoods, Hyde Park, you'll find a lot of the city's rich cultural institutions as well as a lot of the city's Black history locales as well. Every neighborhood has something different to offer with strong communities that support them.

Eat that pizza.

Chicago Deep Dish Pizza

If you've never tried a Chicago deep-dish pizza before, you need to try one while you're here. Folks tend to fiercely defend their favorite deep dish spot, so you'll have to decide for yourself where to go. Plenty of mom-and-pop pizzerias have their own selections which you can find throughout the city. Otherwise, the mainstay chain spots are Lou Malnati's and Giordano's. Personally, I'm team Giordano's all the way–Lou's crusts are too crunchy for my liking.

For more great travel tips and advice, check out 7 Insider Tips to Have the Best Miami Experience Ever.

Amanda Finn
Amanda Finn is an award-winning theater, travel, and lifestyle writer. Read more
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